No matter what stage you're at, who you think your market is, or how much money you have, the very best investment of whatever resources and time you do have should be in getting out of your small town for at least a month and spending time in a city with an international market like New York, Toronto, Vancouver, or pretty much anywhere else.

I highly recommend participating in a program like General Assembly, which I was able to access through the Canadian Tech Accelerator's program. There are a lot of great landing sites for this program. You will get what you put into it. See it as a way to go explore a big market, and use your time to meet as many people as possible who can help you (investors, experts, other entrepreneurs, advisers and mentors).

Why you need to get out

Problems in your little town are not like problems in the rest of the world. You don't have the critical mass required to properly evaluate, launch, and test a product quickly. A good business idea solves a problem you are passionate about for enough people and enough money that you can grow your company.
Going to places where lots of people have problems is inspiring, and can provide you with a more realistic understanding of your market (your product or service might have a wider market application then you thought), your opportunities (what is the easiest way to get to market, for instance), and your challenges (probably includes the fact that you live where you do).
You will be better able to appreciate and communicate the strengths of your hometown if you put some distance between yourself and it. This may not be true for everyone, but I was deeply impressed by the advantage of being inherently under the radar (no matter how much we bragged or made public displays of our skills a daily thing). You may also discover that you'd prefer to move someplace with more opportunity. That's okay too- but you will save yourself time figuring this out right from the beginning.

Pitch your location's advantages

In my hometown, it is easy to build a small, loyal and vociferous army of supporters in media, government and education. Your community will celebrate your successes and build morale within your company. Morale is like currency when you're a startup - people will feel inspired to take risks with you if in doing so they are also gaining the respect and support of their community. In bigger cities this is super hard to achieve.

Compared to big cities, your town may offer low overhead, a strong sense of community, staff loyalty, and a relatively healthy talent pool with less local competition for talent. Winnipeg happens to have the best Maker Space (Assent Works) I have ever seen; it's much better then comparible spaces in Silicon Valley and New York, and much less expensive. You probably have similar gems. Learn to talk about them and brag about them to others; it makes a big difference when you are looking for partners in bigger cities if you can sell your location as well as your ideas.

It's easier to be a big fish in a small pond. In order to conquer the global marketplace you have to become much bigger then you are, and this starts with perception.

My hometown is forgiving of failures, and we want to see people succeed. Learn to be a big fish in your own town and you will have the confidence to become a bigger fish elsewhere. Making a mistake at home will not cost as much or kill your company, so it's easier to take risks.

TIP: It is worth knowing that it's inexpensive to get a mailing address and phone number in the USA as well as a Google Voice account in San Francisco. Adding a New York contact to your business cards and emails is not a horrible idea.

TIP: If you think your business is going to require you to travel regularly (more then once a month) you should strongly consider moving - the economics of paying a lot just to get out of town often does not balance out against the increased overhead in bigger cities, and as a startup you will get a lot more accomplished if you are close to your customers. Don't worry; you can always go home when you make millions of dollars.